著者

Taketo Kojima Ikumi Kawajiri Jun-ichi Nishida Chitoshi Kitamura Hiroyuki Kurata Mirai Tanaka Hiroshi Ikeda Takeshi Kawase

出版者

(社)日本化学会

雑誌

Bulletin of the Chemical Society of Japan (ISSN:00092673)

巻号頁・発行日

pp.20160093, (Released:2016-05-24)

被引用文献数

8

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A series of 2,3-diphenylphenanthro[9,10-b]furans were prepared by the reactions of phenanthrene-9,10-dione with two equivalents of benzylidenetriphenylphosphoranes as a key step. The bis(4-bromophenyl) derivative can be readily lithiated by the action of n-butyllithium in diethyl ether. The corresponding 4-trimethylsilyl and 4-methylthio derivatives were obtained by quenching the dilithio derivative with trimethylsilyl chloride and dimethyl disulfide, respectively. The Buchwald–Hartwig amination of the bromide with diphenylamine afforded the diphenylamino derivative in a good yield. Crystallographic analysis of the parent diphenyl derivative reveals that the phenanthrofuran moiety has a slightly twisted helicene-like structure, and the compound forms a columnar stacking in the crystal. The phenanthrofurans display intense blue fluorescence both in CH2Cl2 and in the solid state. Their electrochemical properties obviously indicate high HOMO energy levels of the furans, as predicted by the density functional theory calculations.

著者

Hiroaki Ozoe Chitoshi Kitamura Hiroyuki Kurata Jun-ich Nishida Takeshi Kawase

出版者

(社)日本化学会

雑誌

Chemistry Letters (ISSN:03667022)

巻号頁・発行日

vol.43, no.9, pp.1467-1469, 2014-09-05 (Released:2014-09-05)

参考文献数

32

被引用文献数

5

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The title imides possessing a planar acenaphthofluoranthene moiety were prepared by the Diels–Alder reaction of diacenaphtho[1,2-b:1′,2′-d]thiophene and maleic anhydride and subsequent treatment with amines. The reaction with maleimide afforded the corresponding 1:2 adduct displaying intense blue fluorescence in solution. Although the imides crystallize yellow needles, their amorphous solids are red. Concentration-dependent 1H NMR spectra of a N-octyl derivative reveal self-aggregation behavior in CDCl3.